Epsilon-(gamma-Glutamyl)-lysine (CHEM035579)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:54:00 UTC
Update Date2026-04-06 12:13:44 UTC
Accession NumberCHEM035579
Identification
Common NameEpsilon-(gamma-Glutamyl)-lysine
ClassSmall Molecule
DescriptionAn N(6)-acyl-L-lysine derivative in which the acyl group is specified as gamma-glutamyl.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
epsilon-(gamma-L-Glutamyl)-L-lysineChEBI
epsilon-(L-gamma-Glutamyl)-L-lysineChEBI
gamma-Glu-epsilon-lysChEBI
gamma-Glutamyl-epsilon-lysineChEBI
L-gamma-Glutamyl-L-epsilon-lysineChEBI
N(6)-L-gamma-Glutamyl-L-lysineChEBI
N(epsilon)-(gamma-Glutamyl)-lysineChEBI
epsilon-(g-L-Glutamyl)-L-lysineGenerator
epsilon-(L-g-Glutamyl)-L-lysineGenerator
g-Glu-epsilon-lysGenerator
g-Glutamyl-epsilon-lysineGenerator
L-g-Glutamyl-L-epsilon-lysineGenerator
N(6)-L-g-Glutamyl-L-lysineGenerator
N(epsilon)-(g-Glutamyl)-lysineGenerator
epsilon-(g-Glutamyl)lysineGenerator
epsilon-(gamma-Glu)-lysHMDB, MeSH
epsilon-(gamma-Glutamyl)lysineHMDB
epsilon-(gamma-Glutamyl)lysine isodipeptideHMDB, MeSH
GGEL peptideMeSH, HMDB
N-epsilon-(gamma-L-Glutamyl)lysineMeSH, HMDB
epsilon-(gamma-Glutamyl)-lysineMeSH, HMDB
Epsilon-(g-Glutamyl)-lysineGenerator, HMDB
N6-L-gamma-Glutamyl-L-lysineHMDB
N6-L-γ-Glutamyl-L-lysineHMDB
Nepsilon(gamma-Glutamyl)lysineHMDB
Nepsilon-(gamma-Glutamyl)-L-lysineHMDB
Nε(γ-Glutamyl)lysineHMDB
Nε-(γ-Glutamyl)-L-lysineHMDB
epsilon-(gamma-L-Glutamyl)lysineHMDB
epsilonN-(gamma-L-Glutamyl)-L-lysineHMDB
γ-Glutamyl-ε-lysineHMDB
ε-(L-γ-Glutamyl)-L-lysineHMDB
ε-(γ-Glutamyl)lysineHMDB
ε-(γ-L-Glutamyl)-L-lysineHMDB
ε-(γ-L-Glutamyl)lysineHMDB
εN-(γ-L-Glutamyl)-L-lysineHMDB
Chemical FormulaC11H21N3O5
Average Molecular Mass275.302 g/mol
Monoisotopic Mass275.148 g/mol
CAS Registry Number17105-15-6
IUPAC Name(2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid
Traditional NameN(6)-L-gamma-glutamyl-L-lysine
SMILESN[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1
InChI KeyJPKNLFVGUZRHOB-YUMQZZPRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Primary aliphatic amine
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.27 g/LALOGPS
logP-4ALOGPS
logP-6.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)9.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.74 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity65.9 m³·mol⁻¹ChemAxon
Polarizability28.48 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-5940000000-d882bed3b5529ecff7f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-6639100000-f6ca1e086349e3426243Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0490000000-072f36ed9a7b3013d059Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2930000000-392395a44df2ae8037f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9500000000-6e7ed98ff09e19e298dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0190000000-58b6ca56f7cccfc512beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aba-1690000000-fc6b7fb17538a52f8f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006w-9700000000-4409c236d141d5814427Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0190000000-87a26493d0e45ab09e99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1930000000-3595f6a3ff829eac51deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-8574eb2f5fa536d0c5abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-0390000000-6d00013244e4fc3d3d9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9430000000-86b20a12b25ddf059e72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9200000000-6238074e2599c8441ec5Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003869
FooDB IDFDB023239
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID5378717
ChEBI ID88494
PubChem Compound ID7015684
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jeitner TM, Bogdanov MB, Matson WR, Daikhin Y, Yudkoff M, Folk JE, Steinman L, Browne SE, Beal MF, Blass JP, Cooper AJ: N(epsilon)-(gamma-L-glutamyl)-L-lysine (GGEL) is increased in cerebrospinal fluid of patients with Huntington's disease. J Neurochem. 2001 Dec;79(5):1109-12.
2. El Nahas AM, Abo-Zenah H, Skill NJ, Bex S, Wild G, Griffin M, Johnson TS: Elevated epsilon-(gamma-glutamyl)lysine in human diabetic nephropathy results from increased expression and cellular release of tissue transglutaminase. Nephron Clin Pract. 2004;97(3):c108-17.
3. Andringa G, Lam KY, Chegary M, Wang X, Chase TN, Bennett MC: Tissue transglutaminase catalyzes the formation of alpha-synuclein crosslinks in Parkinson's disease. FASEB J. 2004 May;18(7):932-4. Epub 2004 Mar 4.
4. Priglinger SG, Alge CS, Kook D, Thiel M, Schumann R, Eibl K, Yu A, Neubauer AS, Kampik A, Welge-Lussen U: Potential role of tissue transglutaminase in glaucoma filtering surgery. Invest Ophthalmol Vis Sci. 2006 Sep;47(9):3835-45.
5. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.